#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222110.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222110
loop_
_publ_author_name
'Li, Rui'
'Ding, Zhen-Yu'
'Wei, Yu-Quan'
'Ding, Jian'
_publ_section_title
2-{4-[(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino]phenyl}acetonitrile
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1296
_journal_paper_doi               10.1107/S1600536809017437
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H14 N2 O4'
_chemical_formula_moiety         'C15 H14 N2 O4'
_chemical_formula_sum            'C15 H14 N2 O4'
_chemical_formula_weight         286.28
_chemical_name_systematic
2-{4-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino]phenyl}acetonitrile
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.51(3)
_cell_angle_beta                 82.30(3)
_cell_angle_gamma                84.54(2)
_cell_formula_units_Z            2
_cell_length_a                   5.204(3)
_cell_length_b                   11.239(3)
_cell_length_c                   12.209(4)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      9.72
_cell_measurement_theta_min      5.50
_cell_volume                     702.9(5)
_computing_cell_refinement       'DIFRAC (Gabe & White, 1993)'
_computing_data_collection       'DIFRAC (Gabe & White, 1993)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       Omega/2-Theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0032
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3217
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        1.320
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0853P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                1610
_reflns_number_total             2609
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ng2579.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2222110
_cod_database_fobs_code          2222110
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5677(3) 0.03464(12) 0.29695(11) 0.0620(4) Uani d . 1 . .
O O2 0.8342(3) 0.19500(12) 0.26775(11) 0.0573(4) Uani d . 1 . .
O O3 0.2465(3) 0.02806(12) 0.43304(11) 0.0639(4) Uani d . 1 . .
O O4 0.7647(3) 0.35124(12) 0.36881(12) 0.0634(4) Uani d . 1 . .
N N1 0.1001(3) 0.22676(14) 0.54592(13) 0.0498(4) Uani d . 1 . .
H H1N 0.074(5) 0.145(2) 0.5335(18) 0.091(8) Uiso d . 1 . .
N N2 -0.9365(5) 0.3352(2) 0.9847(2) 0.1123(9) Uani d . 1 . .
C C1 0.9231(5) 0.0301(2) 0.1573(2) 0.0831(8) Uani d . 1 . .
H H1A 1.0196 0.0754 0.0984 0.125 Uiso calc R 1 . .
H H1B 0.8480 -0.0329 0.1271 0.125 Uiso calc R 1 . .
H H1C 1.0377 -0.0040 0.2090 0.125 Uiso calc R 1 . .
C C2 0.5317(5) 0.1765(2) 0.13934(18) 0.0744(7) Uani d . 1 . .
H H2A 0.3912 0.2203 0.1823 0.112 Uiso calc R 1 . .
H H2B 0.4629 0.1198 0.0986 0.112 Uiso calc R 1 . .
H H2C 0.6268 0.2311 0.0886 0.112 Uiso calc R 1 . .
C C3 0.7107(4) 0.11099(19) 0.21537(16) 0.0573(6) Uani d . 1 . .
C C4 0.4120(4) 0.08606(17) 0.38115(16) 0.0519(5) Uani d . 1 . .
C C5 0.4624(4) 0.20480(16) 0.40360(15) 0.0471(5) Uani d . 1 . .
C C6 0.6901(4) 0.25836(17) 0.34787(15) 0.0477(5) Uani d . 1 . .
C C7 0.3046(4) 0.26618(16) 0.48329(15) 0.0493(5) Uani d . 1 . .
H H7 0.3459 0.3428 0.4941 0.059 Uiso calc R 1 . .
C C8 -0.0785(4) 0.29056(16) 0.62235(15) 0.0472(5) Uani d . 1 . .
C C9 -0.2817(4) 0.23184(17) 0.67757(17) 0.0568(6) Uani d . 1 . .
H H9 -0.2971 0.1528 0.6638 0.068 Uiso calc R 1 . .
C C10 -0.4632(4) 0.28879(18) 0.75328(16) 0.0573(6) Uani d . 1 . .
H H10 -0.5997 0.2476 0.7901 0.069 Uiso calc R 1 . .
C C11 -0.4454(4) 0.40591(18) 0.77514(16) 0.0507(5) Uani d . 1 . .
C C12 -0.2402(4) 0.46434(17) 0.71855(16) 0.0535(5) Uani d . 1 . .
H H12 -0.2253 0.5435 0.7321 0.064 Uiso calc R 1 . .
C C13 -0.0575(4) 0.40860(17) 0.64268(16) 0.0541(5) Uani d . 1 . .
H H13 0.0786 0.4497 0.6055 0.065 Uiso calc R 1 . .
C C14 -0.6446(4) 0.47201(19) 0.85500(16) 0.0608(6) Uani d . 1 . .
H H14A -0.5548 0.5184 0.8994 0.073 Uiso calc R 1 . .
H H14B -0.7541 0.5278 0.8130 0.073 Uiso calc R 1 . .
C C15 -0.8082(5) 0.3952(2) 0.92822(19) 0.0722(7) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C3 . . 118.27(15) ?
C6 O2 C3 . . 118.41(15) ?
C7 N1 C8 . . 127.60(16) ?
C7 N1 H1N . . 112.8(15) ?
C8 N1 H1N . . 119.5(15) ?
C3 C1 H1A . . 109.5 ?
C3 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C3 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C3 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
O2 C3 O1 . . 110.49(15) ?
O2 C3 C1 . . 106.90(17) ?
O1 C3 C1 . . 105.58(18) ?
O2 C3 C2 . . 109.82(18) ?
O1 C3 C2 . . 110.28(17) ?
C1 C3 C2 . . 113.65(19) ?
O3 C4 O1 . . 117.85(16) ?
O3 C4 C5 . . 125.29(18) ?
O1 C4 C5 . . 116.83(16) ?
C7 C5 C4 . . 120.65(17) ?
C7 C5 C6 . . 118.69(16) ?
C4 C5 C6 . . 120.53(17) ?
O4 C6 O2 . . 118.25(17) ?
O4 C6 C5 . . 125.76(19) ?
O2 C6 C5 . . 115.95(15) ?
N1 C7 C5 . . 126.03(17) ?
N1 C7 H7 . . 117.0 ?
C5 C7 H7 . . 117.0 ?
C9 C8 C13 . . 119.39(18) ?
C9 C8 N1 . . 117.65(16) ?
C13 C8 N1 . . 122.96(17) ?
C8 C9 C10 . . 120.69(17) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
C11 C10 C9 . . 120.89(19) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 117.88(19) ?
C10 C11 C14 . . 122.30(19) ?
C12 C11 C14 . . 119.80(17) ?
C13 C12 C11 . . 121.86(17) ?
C13 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
C12 C13 C8 . . 119.30(18) ?
C12 C13 H13 . . 120.4 ?
C8 C13 H13 . . 120.4 ?
C15 C14 C11 . . 114.09(18) ?
C15 C14 H14A . . 108.7 ?
C11 C14 H14A . . 108.7 ?
C15 C14 H14B . . 108.7 ?
C11 C14 H14B . . 108.7 ?
H14A C14 H14B . . 107.6 ?
N2 C15 C14 . . 179.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.352(2) ?
O1 C3 . 1.439(2) ?
O2 C6 . 1.356(2) ?
O2 C3 . 1.426(2) ?
O3 C4 . 1.210(2) ?
O4 C6 . 1.205(2) ?
N1 C7 . 1.316(2) ?
N1 C8 . 1.412(2) ?
N1 H1n . 0.96(2) ?
N2 C15 . 1.125(3) ?
C1 C3 . 1.500(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.505(3) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C4 C5 . 1.438(2) ?
C5 C7 . 1.371(3) ?
C5 C6 . 1.444(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.371(3) ?
C8 C13 . 1.386(3) ?
C9 C10 . 1.379(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.378(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.383(3) ?
C11 C14 . 1.508(3) ?
C12 C13 . 1.377(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.444(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1n O3 . 0.97(2) 1.94(2) 2.710(3) 135(2) yes
C7 H7 O4 . 0.93 2.49 2.816(3) 100 no
C9 H9 O3 2_556 0.93 2.41 3.292(3) 159 no
C13 H13 O4 2_666 0.93 2.51 3.208(3) 132 no
C14 H14B O4 2_566 0.97 2.51 3.343(3) 143 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 O2 C3 O1 . . . . -49.2(2) ?
C6 O2 C3 C1 . . . . -163.65(17) ?
C6 O2 C3 C2 . . . . 72.6(2) ?
C4 O1 C3 O2 . . . . 46.8(2) ?
C4 O1 C3 C1 . . . . 162.08(18) ?
C4 O1 C3 C2 . . . . -74.8(2) ?
C3 O1 C4 O3 . . . . 162.19(19) ?
C3 O1 C4 C5 . . . . -19.5(3) ?
O3 C4 C5 C7 . . . . -5.6(3) ?
O1 C4 C5 C7 . . . . 176.25(17) ?
O3 C4 C5 C6 . . . . 170.2(2) ?
O1 C4 C5 C6 . . . . -7.9(3) ?
C3 O2 C6 O4 . . . . -158.33(18) ?
C3 O2 C6 C5 . . . . 23.8(2) ?
C7 C5 C6 O4 . . . . 4.2(3) ?
C4 C5 C6 O4 . . . . -171.73(19) ?
C7 C5 C6 O2 . . . . -178.17(16) ?
C4 C5 C6 O2 . . . . 5.9(3) ?
C8 N1 C7 C5 . . . . -174.51(18) ?
C4 C5 C7 N1 . . . . 0.3(3) ?
C6 C5 C7 N1 . . . . -175.62(18) ?
C7 N1 C8 C9 . . . . 178.79(18) ?
C7 N1 C8 C13 . . . . -0.7(3) ?
C13 C8 C9 C10 . . . . -0.4(3) ?
N1 C8 C9 C10 . . . . -179.96(18) ?
C8 C9 C10 C11 . . . . 0.1(3) ?
C9 C10 C11 C12 . . . . 0.2(3) ?
C9 C10 C11 C14 . . . . 178.25(19) ?
C10 C11 C12 C13 . . . . -0.1(3) ?
C14 C11 C12 C13 . . . . -178.27(19) ?
C11 C12 C13 C8 . . . . -0.2(3) ?
C9 C8 C13 C12 . . . . 0.4(3) ?
N1 C8 C13 C12 . . . . 179.96(18) ?
C10 C11 C14 C15 . . . . 16.7(3) ?
C12 C11 C14 C15 . . . . -165.3(2) ?
C11 C14 C15 N2 . . . . -7E1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655794
